JOHN JAY COLLEGE OF CRIMINAL JUSTICE
The City University of New York
CHEMISTRY 201 ORGANIC CHEMISTRY --- Fall 2012
Sections 01-08
Instructor: Elise Champeil
Office Location: 5.66.15
Contact hours: Monday 10-11 AM
Phone: 646-557-4502
Email address: echampeil@jjay.cuny.edu
Laboratory/Recitation Instructors and their contacts:
Recitation Instructor: Dr. Gloria Proni - gproni@jjay.cuny.edu
Elaan Luckasiewicz- elaanluk@yahoo.com
Amanda Vasquez- avpink.vasquez@gmail.com
Alison Domzalski- calisonche@gmail.com
Course Description
Today's qualified forensic scientist must acquire a capacity for logical reasoning, an imaginative approach to solving problems and a
flexibility that allows adaptation to a changing world. CHEM 201 aims to develop these qualities in the area of introductory organic
chemistry. Goals of the course are, also, essential experimental laboratory skills and fundamental knowledge in the foundations of
organic chemistry.
In particular, CHEM 201 is a systematic introduction to the chemistry of carbon compounds. It encompasses theory and reactions of
hydrocarbons and functional group derivatives. Included are bonding and structure, nomenclature, stereochemistry, synthesis,
mechanism, and spectroscopic analysis. The laboratory work focuses on techniques of synthesis, isolation, purification, and analysis.
The laboratory component of this course consists of fourteen double-John Jay sessions over the semester. The recitations, held in a
single John Jay period weekly, will be dedicated to explaining difficult topics, answering student questions, reviewing the material
discussed in the lectures.
Learning Outcomes
Assessed by: exams' and laboratory's performances and/or evaluation of notebook data and lab reports and/or lab tests.
The student will demonstrate the ability to use the appropriate problem-solving techniques to solve a scientific problem such as an
organic synthesis comprised of one or more steps, or a determination of the structure of a compound based on spectroscopy (IR, NMR,
MS) and/or chemical evidence.
When conducting a laboratory experiment, the student will follow written procedures commonly used in the organic lab (such as reflux,
distillation, extraction, recrystallization, and melting-point determination) accurately and safely. When completing a lab report, the
student will apply the scientific method correctly by being able to state a hypothesis, take careful measurements, estimate uncertainties
and draw appropriate conclusions based on gathered data and scientific principles.
The student will explain observable phenomena using appropriate scientific theories, such as writing a reaction mechanism consistent
with observed facts or utilizing appropriate structures to represent different types of organic molecules and species.
Reasoning
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Predict the major product in an organic reaction, such as those involving hydrocarbons, alcohols, alkyl halides and alkenes
Write synthetic schemes for the production of different classes of these compounds
Analyze spectroscopic data to solve the structures of organic compounds.
Perform retrosynthetic analysis
Analyze spectroscopic data to solve the structures of organic compounds.
Predict the optical activities and stereochemistry properties for different classes of compounds
Analyze the structure of a given compound and predict the type of bonding, hybridization state, and effect of the structure on
the physical properties of such compound.
Draw conclusions from experimental data gathered during laboratory sessions.
Knowledge
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Recognize main functional groups in organic compounds
Name organic compounds using the IUPAC nomenclature
Recognize nucleophiles, electrophiles and their reactivity in order to predict the course of a reaction.
Interpret laboratory instructions, safety sheets and experimental protocols
Define the structures and properties of organic compounds
Describe basic organic chemistry mechanisms (SN1, SN2, E1, E2 …).
Explain the theory behind basic spectroscopic methods
Use appropriate current technology in the laboratory to obtain data und understand the impact that recent technologies have
on the field
Practical skills
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Apply basic synthetic skills
Illustrate basic spectroscopic techniques
Standardize and operate laboratory instruments to identify reactants and products and to separate mixtures of compounds
Obtain information about chemical compounds from all possible sources;
Apply this information for the safe handling, use and disposal of such compounds in a safe and environmentally responsible
manner
Communication

Give small presentation on organic compounds
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
Prepare laboratory reports in accordance with current forensic reports' styles
Course prerequisites or co-requisites
ENG 101 and CHE 104
Requirements / Course Policies
Students enrolled in this course are required to attend all lecture, recitation, and laboratory sessions of the section for which they
registered. There are two lecture sessions, one recitation session, and one laboratory session per week. If a student needs to miss
classes he/she may do so, but the instructor may ask to withdraw from the course. More than 3 absences in the labs, lectures or
recitation classes will result in an unofficial withdrawal grade. The information missed is vital to your future profession. Attendance,
enthusiasm, and active class participation are observed, recorded, and reflected in the student’s final grade. Late arrival to the lab
WILL NOT be tolerated (students will be penalized if late): such behavior has direct consequences upon the safety in the lab.
Attendance is taken solely from roll sheets circulated at the beginning and/or end of each session or by the clickers. Lateness or early
departure counts as ½ absence. Students missing more than 30 minutes of a session will be counted as absent. Obviously there is no
penalty for students when classes are canceled.
Required Texts
Lecture Text:
Organic Chemistry,10th Edition, by Solomons, John Wiley and Sons, Incorporated 2009
You have the flexibility of buying the book in different formats, each at different prices.
The ISBN of the cheapest version with WileyPlus is 9780470932742: this is the binder-ready version of the textbook with a WileyPLUS
code.
Do not throw away the WileyPlus registration card, as resources found in WileyPlus will be used in class and homework will be
assigned online.
John Jay Bookstore
1.) Text with WileyPlus,
(standard version of the book packaged with WileyPlus)
2.) BinderReady Text with WileyPlus,
(3 hole punched, color pages, just like the regular book, without the binding. You can carry chapters with you to class or insert
in a binder of your choice)
www.wileyplus.com
3 .) WileyPlus (buy directly online from www.wileyplus.com)
(Here you do not get a physical book, just access to online ebook, all learning tools, and homework problems. )
Lab Manual: (The lab manual must be brought to each laboratory session.)
Introduction to Organic Laboratory Techniques: A Microscale Approach, 4th Edition
Donald L. Pavia | Gary M. Lampman | George S. Kriz | Randall G. Engel
Necessary for recitation and during the lecture exams: Molecular structure models [the instructor recommend models from
HGS Molecular Structure model but you are free to get different models that satisfy you].
Other required material (to be brought to each laboratory session):
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Splash-resistant safety goggles or safety glasses meeting the ANSI Z87.1-1989 standard. All students must wear safety
glasses or goggles in lab. Students requiring corrective lenses must wear safety glasses or goggles over the corrective
lenses.
A non-programmable scientific calculator that can be removed from its case (available at most electronic stores).
The John Jay library (212-237-8200) owns several copies of the textbook and so does the Math and Science Tutoring Center (646-5574595). In addition, videos have been recorded of the majority of the lecture classes for your review in case you have missed classes
and are available in the Math and Science Tutoring Center.
Grading
This course has three components -- lecture, recitation, and laboratory. Each component has a separate grading policy, which
contributes a percentage to the overall course grade. In general, the course grade is the sum of the grades earned in the lecture (60%)
recitation (including homework and participation during recitations: 15%) laboratory (20%) sessions and ACS exam (5%). However,
since the lab sessions are an integrated component of the course, where lab safety skills and dexterity are taught for use in subsequent
science courses, for safety reasons, a minimum lab grade of 60% is required to pass the course. In order to pass the lecture portion
of the course a minimum of 60% in the four lecture exams is necessary. Unethical/unprofessional conduct will result in a failing
course grade and referral for additional action.
Lecture: During the lecture sessions, four exams are given (each of them counts 20% of the lecture grade and last 1 hour and 05
minutes). There are no make-up exams. Unexcused absences from exams will result in a grade of zero. Excused absences will not
lead to a penalty but remaining exams will be weighted correspondingly more. Missing three (3) exams automatically constitutes a
grade of F for the course. During the final exam’s week the American Chemical Society (ACS) standardized test (which lasts two hours)
is given which counts as 5% of the final. It is a cumulative exam and it needs to be taken in the date dictated by the instructor (based
on ACS regulations all students need to take the exam together). If a student miss the ACS standardized test in the final week of
exams (with an excused absence) and he is passing the course up to that point, he will receive a grade that correspond to the average
of the other four exams. If he is missing the ACS exams during the final week of exams and he is not passing the course up to that
point a grade of "F" will be assigned. THERE WILL BE NO MAKE-UPS OF THE ACS EXAM or OF ANY OTHER EXAMS. It is
important to understand that it is students’ responsibility to come to class and take the exams. During the exams books remain
closed. A non-programmable, scientific calculator may be used during exams if it is removed from its case.
Recitation and Homework: During the recitation sessions, students are encouraged to participate in discussions and activities
related to the lecture material and homework. Active participation by all students benefits all students, providing varying approaches to
mastering the subject material, incentive, and progress evaluation. Consequently, absences or failure to meaningfully participate will
result in a significant course grade penalty. Students’ grade will be based on the homework assigned by the recitation/lecture
instructors (10%) and participation/attendances in the recitation class (5%). Students, during recitation and lecture sessions, are
required to come to the board and do exercises in front of their colleagues in order to get credit for their participation. No computerbased homework will be corrected or graded if handed in a paper copy.
Laboratory:
Pre lab questions
Post lab questions
Safety
8-15 points
8-15 points
5-10 points
Results/observations
15-25 points
Calculations
5-15 points
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References
must
be
included.
All results must be clearly
stated and all observations
recorded.
Correct units must be used.
All yields must be reported.
All numbers must be
Explanation/discussion/conclusion
30-50 points
explained
This is a crucial part of the
lab report.
Detailed explanations of all
your
results
and
observations must be
included.
Your writing must be
concise and easy to
understand.
The conclusion has to be
thorough and you must
demonstrate that you
understood the principles of
the lab.
Remember: There is no wrong or right. If results are different from what is expected DO NOT INVENT. Instead, try to find logical
explanations for what happened. This will be taken into account and your grade will not suffer from it, as long as you provide a
reasonable justification. This is the opportunity to develop your critical thinking abilities and your writing skills.
Reports written by Forensic Scientists must be clear, concise, and unambiguous. Consequently, when a question in the
test/quiz/laboratory report assigned requires a written explanation, spelling, grammar, and clarity of expression will be considered in
determining the “correctness” of the answer proffered. It is important that careful attention is directed to writing what you mean and
meaning what you write. If the grade on the first two laboratory reports is below B, students will be referred to the Writing Center
Services (212-237-8659).
College Wide Policies for Undergraduate Courses (see the Undergraduate Bulletin, Chapter IV
Academic Standards)
Americans with Disabilities Act (ADA) Policies
Sample syllabus statement: “Qualified students with disabilities will be provided reasonable academic accommodations if determined
eligible by the Office of Accessibility Services (OAS). Prior to granting disability accommodations in this course, the instructor must
receive written verification of a student’s eligibility from the OAS which is located at L66 in the new building (212-237-8031). It is the
student’s responsibility to initiate contact with the office and to follow the established procedures for having the accommodation notice
sent to the instructor.”
Source: Reasonable Accommodations: A Faculty Guide to Teaching College Students with Disabilities, 4th ed., City University
of New York, p.3.
(http://www.jjay.cuny.edu/studentlife/Reasonable_Accommodations.pdf)
Statement of the College Policy on Plagiarism
Plagiarism is the presentation of someone else‘s ideas, words, or artistic, scientific, or technical work as one‘s own
creation. Using the ideas or work of another is permissible only when the original author is identified. Paraphrasing and
summarizing, as well as direct quotations require citations to the original source.
Plagiarism may be intentional or unintentional. Lack of dishonest intent does not necessarily absolve a student of
responsibility for plagiarism.
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It is the student‘s responsibility to recognize the difference between statements that are common knowledge (which do not
require documentation) and restatements of the ideas of others. Paraphrase, summary, and direct quotation are acceptable
forms of restatement, as long as the source is cited.
Students who are unsure how and when to provide documentation are advised to consult with their instructors. The Library
has free guides designed to help students with problems of documentation. (John Jay College of Criminal Justice
Undergraduate Bulletin, http://www.jjay.cuny.edu/academics/654.php, see Chapter IV Academic Standards)
Ethics
Ethics principles in chemical research will be discussed during the lecture sessions.
Tutoring
Although a considerable amount of remediation is done during the recitation portion of the course, when necessary the Science
Department generally provides -- on a first come, first served basis -- tutoring to students requesting such help at the Math and Science
Tutoring Center. Scheduled weekly appointments are encouraged. “Crash” sessions immediately before a quiz or exam are
discouraged. Although participation in these sessions is not required, most students find them helpful. There is no charge for tutoring.
Course Calendars: in this order lecture, laboratory and recitation
Last day to drop the class without academic penalty: Friday November 9 th!
SESSION
1
DATES
AugustSeptember
28-August
2
30-August
3
4-September
4
6-September
5
11-September
6
13-September
7
8
20-September
27-September
9
October
2-October
10
11
12
04
09
11
TOPICS
CHAPTER
Carbon Compounds and Chemical
Bonds
Carbon Compounds and Chemical
Bonds
Hydrocarbons: Representative
alkanes, etc. (no 2.15 on)
Hydrocarbons: Representative
alkanes, (no 2.15 on)
An introduction to organic reaction:
Acids and bases
An introduction to organic reaction:
Acids and bases
EXAM 1
Alkanes: Nomenclature,
conformational analysis, etc
1
Alkanes: Nomenclature,
conformational analysis, etc.
Stereochemistry: Chiral molecules
Stereochemistry: Chiral molecules
Stereochemistry: Chiral molecules
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1
HOMEWORK
Wiley Plus
2
2
Wiley Plus
3
3
Wiley Plus
3
4
4
Wiley Plus
5
5
5
Wiley Plus
13
16
14
18
15
23
16
25
17
November
30
18
19
01
06
20
08
21
13
22
23
15
20
24
27
25
29
26
December
04
27
28
FINAL
WEEK
06
11
Tuesday
Thursday
28-Aug
30-Aug
04-Sep
06-Sep
11-Sep
13-Sep
02-Oct
20-Sep
Ionic Reactions-Nuclophilic
Substitution and elimination etc
Ionic Reactions-Nuclophilic
Substitution and elimination etc
Alkenes and Alkynes I: Properties
and Synthesis. Etc.
Alkenes and Alkynes I: Properties
and Synthesis. Etc.
6
Alkenes and Alkynes I: Properties
and Synthesis. Etc.
EXAM 2
Alkenes and Alkynes II: Addition
Reactions
Alkenes and Alkynes II: Addition
Reactions
Alkenes and Alkynes II: Addition
Reactions
Mass spectroscopy
IR spectroscopy
7
6
7
7
8
8
Wiley Plus
2.15
9
Nuclear Magnetic Resonance and
Mass Spectrometry: Tools etc.
Radical Reaction
EXAM 3
ACS EXAM – NO MAKE UP
EXAMS GIVEN
9
Check - In, Lab Safety,
Procedures, Glassware
Exp 2A, 2C, 3A Solubility,
Crystallization, Melting Point
Determination
Exp 4B,C,E Extraction
Exp 6B Simple and
Fractional Distillation,
Refractive Index Analysis
Wiley Plus
8
Nuclear Magnetic Resonance and
Mass Spectrometry: Tools etc.
Nuclear Magnetic Resonance and
Mass Spectrometry: Tools etc.
Laboratory Experiment
Wiley Plus
9
Wiley Plus
10
Procedure
Pages
Required Reading
n/a
Techniques 1, 2, 3, 4, 29
13 - 25
Techniques 8.3, 8.5, 9.2, 9.4, 9.7, 9.8, 10.1, 10.2,
11.1, 11.2, 11.3, 11.8, 11.9
32 - 41
Techniques 12.1 - 12.6, 12.8 - 12.10
51 - 57
Techniques 14.1 - 14.3, 15.1 - 15.3, 24
Page 7 of 9
09-Oct
27-Sep
16-Oct
04-Oct
23-Oct
11-Oct
30-Oct
18-Oct
06-Nov
25-Oct
13-Nov
01-Nov
20-Nov
08-Nov
27-Nov
15-Nov
04-Dec
29-Dec
11-Dec
06-Dec
Exp 5A,B Thin-Layer
Chromatography
Exp 5C Thin-Layer
Chromatography
Exp 14 (+) and (-) Carvones
Extraction from Caraway
and Spearmint
Exp 15 (+) and (-) Carvones
HPLC and IR Analysis
Exp 35A OxidationReduction Scheme:
Borneol, Camphor,
Isoborneol, IR analysis
Exp 35B OxidationReduction Scheme: Borneol,
Camphor, Isoborneol, IR
analysis
Exp 21A, B Nucleophilic
Substitution Reactions:
Competitive Nucleophiles
Exp 21A, B Nucleophilic
Substitution Reactions:
Competitive Nucleophiles
Exp 54C,H Tests for
Organic Substances:
Unsaturation and Alcohols
Lab Final, Check out
Tuesday
Thursday
Laboratory Experiment
42 - 46
Technique 20
Technique 11, 20
46 - 48
108 - 116
Techniques 7.10, 12.4, 12.9, 18
119 - 131
Techniques 21, 25
288 - 295
Techniques 7.1 - 7.4, 7.10, 8.3, 9.7, 9.8, 12.4, 25
295
Techniques 7.1 - 7.4, 7.10, 8.3, 9.7, 9.8, 12.4, 25
180 - 187
Techniques 7.2, 7.4, 7.5, 7.8, 12.5, 12.9, 12.11
187
Technique 22
466 – 469
486 - 491
Technique 10
n/a
Procedure
Pages
Review all materials
Required Reading
Last day to drop the class without academic penalty: Friday November 9 th!
TUESDAY
THURSDAY
28-Aug
30-Aug
04-Sep
06-Sep
11-Sep
13-Sep
02-Oct
20-Sep
09-Oct
27-Sep
MATERIAL TO BE
REVIEWED
Carbon compounds and
chemical bonds
Hydrocarbons:
representative alkanes, etc.
An introduction to organic
reaction: Acids and bases
Alkanes: nomenclature,
conformational analysis, etc
Alkanes: nomenclature,
conformational analysis, etc
Page 8 of 9
16-Oct
04-Oct
23-Oct
11-Oct
30-Oct
18-Oct
06-Nov
25-Oct
13-Nov
01-Nov
20-Nov
08-Nov
27-Nov
15-Nov
04-Dec
29-Nov
11-Dec
06-Dec
Stereochemistry: chiral
molecules
Ionic reactions-nucleophilic
substitution and elimination
Ionic reactions-nucleophilic
substitution and elimination
Alkenes and Alkynes I:
Properties and Synthesis.
Alkenes and Alkynes II:
Properties and Synthesis.
IR spectroscopy
Nuclear Magnetic
Resonance and Mass
Spectrometry: Tools etc.
Nuclear Magnetic
Resonance and Mass
Spectrometry: Tools etc.
Radical Reaction
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